CN102573817A - Transdermal therapeutic system comprising 4-n-butylresorcinol - Google Patents

Transdermal therapeutic system comprising 4-n-butylresorcinol Download PDF

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Publication number
CN102573817A
CN102573817A CN2010800454733A CN201080045473A CN102573817A CN 102573817 A CN102573817 A CN 102573817A CN 2010800454733 A CN2010800454733 A CN 2010800454733A CN 201080045473 A CN201080045473 A CN 201080045473A CN 102573817 A CN102573817 A CN 102573817A
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Prior art keywords
transdermal therapeutic
therapeutic system
self
substrate
beauty treatment
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CN2010800454733A
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Inventor
卡尔-海因茨·韦勒尔
路哲尔·科尔比
卡特琳·舍纳
赖纳·沃尔贝
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Beiersdorf AG
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Beiersdorf AG
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Priority to CN201610333691.6A priority Critical patent/CN105997948A/en
Publication of CN102573817A publication Critical patent/CN102573817A/en
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/42—Use of materials characterised by their function or physical properties
    • A61L15/44—Medicaments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
    • A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
    • A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
    • A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
    • A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
    • A61K9/7061—Polyacrylates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
    • A61K9/7076—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising ingredients of undetermined constitution or reaction products thereof, e.g. rosin or other plant resins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/216—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with other specific functional groups, e.g. aldehydes, ketones, phenols, quaternary phosphonium groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/404—Biocides, antimicrobial agents, antiseptic agents

Abstract

A transdermal therapeutic system comprising 4-n-butylresorcinol as an active ingredient.

Description

The transdermal therapeutic system that comprises the 4-n-butyl resorcinol
Technical field
The present invention relates to comprise transdermal therapeutic system, the self-adhering type plane binder of 4-n-butyl resorcinol, particularly beauty treatment is used and pharmaceutical plaster.
Background technology
The pigment cell is the sedimentary reason of skin pigment, and said pigment cell is present in the epidermis orlop (basal layer), at the cell of the other formation pigment of looking skin type and deciding to occur of basal cell accidental or multiplely.
The pigment cell comprises the chromatoplast as the characteristic organelle, in chromatoplast, forms pigment.First and foremost under situation about stimulating through ultraviolet, pigment acutely forms.Pigment finally is transferred to horny layer (horn cell) through the active layer (keratinocyte) of epidermis, and causes how many significantly brown to memnonious skin colors.
Pigment forms as the end-product of oxidizing process; In oxidizing process, tyrosine is converted into rubescent brown-black element being converted into through a plurality of intermediate under the assistance of tryrosinase under brown to memnonious eumelanin (DHICA (dihydroxy indole carboxylic acid)-pigment and DHI (dihydroxy indole)-pigment) or the participation at sulfur-containing compound.DHICA-pigment and DHI-pigment produce through common intermediate DOPA quinone and DOPA chromium.DOPA chromium partly is converted into indole-5 in the presence of other enzymes, 6-quinone-carboxylic acid or indole-5, and the 6-quinone thus, produces said two kinds of eumelanins.
The generation of pigment is carried out through intermediate product DOPA quinone and cysteinyl dopa especially.(the ommatidium associated transcription factor MITF) is controlled through idiosyncratic transcription factor in the expression of pigment synzyme.Except the synthetic enzymatic processes of described pigment, generation also is important to other protein for pigment in the chromatoplast.As if at this, so-called p-protein has important function, but wherein, exact function is still indeterminate.
The synthetic process of pigment, the transfer of chromatoplast during the skin pigment deposition, its residual and decomposition in epidermis also have the decomposition of pigment all significant in above-described pigment cell.Confirmed the PAR-2-receptor for chromatoplast from the pigment cell be transferred to keratinocyte be important (people such as M.Seiberg, 2000, J.Cell.Sci., 113:3093-101).
In addition, the size and dimension of chromatoplast influences its light scattering character and so cutaneous color outward appearance.Therefore,, find self-existent spherical chromatoplast greatly, and for white situation for Black African's situation, discovery be the less chromatoplast that occurs with group.
The problem of skin pigment over-deposit has multiple reason; And be the concomitant symptom of many biological processes, for example ultraviolet radiation (for example sunburn, freckle (Ephelides)), genetic predisposition, skin wound are being cured or during healing (pigment over-deposit after the inflammation) or the cicatrix pigmentation during skin aging (for example senile plaque (Lentigines seniles)).
After the inflammatory reaction, the pigmentary system of skin reacts, and is attended by the opposite reaction of part.This both can cause pigment over-deposit after the inflammation, also can cause pigmentation not enough.Albinism often follows idiosyncrasy, lupus erythematosus and psoriasis to occur after the inflammation.The differential responses form of the pigmentary system of human skin after inflammatory phenomena do not understood yet fully.
The problem of pigment over-deposit often comes across more dark skin type after the inflammation.Special, the problem of pseudofolliculitis barbae for male coloured race (Pseudofollikulitis barbae) is common, the cicatrix pigmentation that this problem follows or cause the beauty treatment aspect not expect.Pigment over-deposit after the form of form of chloasma (melasma) (producing in Asia women face and breast cervical region especially) and the irregular pigmentation of skin also belongs to inflammation.In addition, pigment was excessive after black eye also were regarded as a kind of inflammation of form, and wherein, potential inflammation takes place with subclinical mode usually.
In many cases, it is even more serious that the cicatrix pigmentation receives the influence of sunlight (ultraviolet) after this inflammation, but the inflammation (sunburn) that can not cause ultraviolet to cause.
Opposing sedimentary effective ingredient of skin pigment and preparation are known.Basically be based on the ingredients of hydroquinone in the practical application, said ingredients just demonstrates its effect on the one hand after using several weeks, and on the other hand, it is former thereby worrying from toxicity that said ingredients is crossed long application.People such as Albert Kligman have researched and developed so-called Triformula (three-in-one prescription), its represent 0.1% retinoic acid, 5.0% hydroquinone, 0.1% dexamethasone combination (A.Kligman, 1975, Arch.Dermatol., 111:40-48).Yet irreversible variation has dispute to said preparation in the skin pigment system owing to causing.
In addition; Use the decortication method/method of peeling (chemistry and physics " peeling/Exfoliating Scrub (Peeling) "); Yet the decortication method/method of peeling belongs to inflammatory reaction usually, and since after the inflammation that occurs subsequently the pigment over-deposit and even can cause more serious pigmentation (but not the pigmentation that reduces).The characteristic of all these common methods (its also be used to treat inflammation after pigment over-deposit) is important side effect.
For example be well known that cosmetic preparation with 4-n-butyl resorcinol by EP1490017.
The 4-n-butyl resorcinol, CAS [18979-61-8] is characterised in that following chemical constitution:
Figure BDA0000151405540000031
The 4-n-butyl resorcinol also is known as Rucin or Lucin.The 4-n-butyl resorcinol suppresses chromogenesis, and mode is: the 4-n-butyl resorcinol suppresses synthetic (pigment generation) required enzyme-network propylhomoserin enzyme of pigment.The 4-n-butyl resorcinol at first suppresses chromogenesis, stops then to cause the strong painted melanic formation of mole.
The shortcoming of 4-n-butyl resorcinol aspect ingredients is beauty treatment usefulness or the dermatological preparation variable color that it tends to make himself and comprises it.
Transdermal therapeutic system (" TTS ") is known.Only discharge about 10% to 20% of plaster effective ingredient useful load between the shortcoming of TTS is usually in use.(Kommentar zum
Figure BDA0000151405540000041
Arzneibuch; Wissenschaftliche Verlagsgesellschaft Stuttgart; Stand:Aktualisierungslieferung 2009 (European Pharmacopoeia guide for use; Stuttgart Science Press, version: latest edition 2009)).
Summary of the invention
Target of the present invention is to improve insufficient prior art.
Beat all and those skilled in the art can't predict is, the drawback of said prior art is able to eliminate as the transdermal therapeutic system of effective ingredient through having the 4-n-butyl resorcinol.
For obtain to be used to treat skin pigment disorderly comprise 4-butyl-resorcinol and effective self-adhering type plaster that have best release property; Preparation has the different self-adhering type matrix system of 1% effective ingredient, and after 24 hours, on Corii Sus domestica, comes the release characteristics of test matrix system by Frantz cell (Franzscher Zellen):
Based on non-polar substrate (KA) synthetic and natural rubber,
Based on the wet adhesive film (FKF) of the polarity of poly propenoic acid vinyl alcohol,
Based on the non-polar substrate (PAC) of acrylic copolymer,
Based on the polarity anhydrous gel substrate (WFG) of poly propenoic acid vinylpyrrolidone,
Nonpolar polyisobutylene substrate (PIB),
Based on agar/polyacrylic polar water gel-type vehicle (WG).
The effective ingredient of different substrates system discharges the result:
(KA) (FKF) (PAC) (WFG) (PIB) (WG)
7.4％ 17.8％ 18.1％ 20.6％ 22.2％ 34.0％
Based on above-mentioned PRELIMINARY RESULTS, select nonpolar polyisobutylene substrate and polar water gel-type vehicle to be used for the further optimization Test that discharges about the 4-n-butyl resorcinol.
Effective ingredient discharges and can preferably control through the layer thickness of TTS.
For two kinds of system PIB and WG, preparation has 1.00,0.75,0.50,0.30 and the sample of 0.15mm layer thickness and making an experiment respectively.
The effective ingredient of different substrates layer thickness discharges the result:
1.00mm 0.75mm 0.50mm 0.30mm 0.15mm
(PIB) 22.2％ 27.4％ 26.7％ 42.7％ 46.4％
(WG) 34.0％ 48.3％ 41.8％ 66.2％ 56.8％
Discharge the compromise proposal between the availability of self-adhering type plaster of percentage ratio, the absolute burst size of effective ingredient and finished product as effective ingredient; What consider for two matrix systems is between 1.00mm and the 0.01mm, preferred 0.50 and 0.20mm between and the layer thickness of preferred quite especially 0.30mm.Specifically, unexpectedly demonstrate than the higher release of common plaster application degree with about 65% effective ingredient based on the self-adhering type plaster of polar water gel according to the present invention.
In the said scope of the PIB-matrix system also being introduced effective ingredient release, proceed test through adding raising hydrophilic common additives of substrate and common penetrating agent.
With the matrix phase ratio of filling without cellulose, the cellulose of interpolation 35% is not producing obvious difference aspect the effective ingredient release in PIB substrate.
As common penetrating agent, in corresponding PIB-substrate, add 5% isopropyl palmitate (IPP) or 5% isopropyl myristate (IPM) respectively, and the release property of the 4-n-butyl resorcinol of the end-product of the 0.30mm layer thickness of confirming to make thus.
The effective ingredient of the PIB substrate of different penetrating agents discharges the result:
PIB-substrate adds 5%IPP PIB-substrate adds 5%IPM
The release of 4-n-butyl resorcinol 33.2％ 61.3％
Unexpectedly, adding 5%IPM demonstrates and adds equivalent penetrating agent IPP and compare and almost double so high PIB-substrate effective ingredient and discharge.
4-n-butyl resorcinol for nonpolar PIB-substrate about 61% discharges, and the polar water gel-type vehicle can reach about 65% the similar order of magnitude.
The example of the preparation of polarity self-adhering type hydrogel matrix is introduced in DE10260872 to some extent.
The example of the preparation of nonpolar self-adhering type PIB-substrate is introduced in EP 1335755 to some extent.
Be suitable as according to of the present invention have that best effective ingredient discharges be used to treat disorderly polarity of skin pigment and nonpolar self-adhering type plaster carrier material be all practicable planar layer materials, such as fabric, thin film, non-woven fabrics etc.For the situation of non-woven fabrics, be preferably the very little so-called non-woven of layer thickness especially, this is because the very little non-woven of layer thickness visually almost can't see with respect to skin on substrate.Preferred especially use as thin as a wafer (layer thickness is lower than 100 μ m), softish and be clear to translucent thin polymer film, the polyurethane film that particularly makes by aqueous dispersion.
Yet also can use the thin film of processing by every other known polymeric film, for example polyethylene, ethyl vinyl acetate etc.For polyisobutylene substrate, when use has 5933.5g/m 2* 24h (sticking fine), 1509.9g/m 2* 24h (polyurethane) is to 25.7g/m 2* (water vapour transmission rate WVTR) during visibly different carrier material, does not find that effective ingredient release aspect is significantly different to the water vapor permeation rate of 24h (polyethylene).In the case, reason is that conduct is the hydrophobicity of PIB-substrate for the WVTR determiner.Yet, in PIB-substrate, use hydrophilic filler for example when cellulose or polyacrylic acid derivative, the carrier material of different WVTR discharges determiner as effective ingredient can become important once more.
For the situation of hydrogel, effective ingredient discharges the strong influence of the WVTR that can receive employed carrier material.For example, the sample that the sample that has a sticking fine carrier demonstrates than has PU (polyurethane)-carrier exceeds 14% effective ingredient and discharges.
Because it is transparent translucent until at most according to hydrogel matrix of the present invention and polyisobutylene substrate; Visually discernable hardly with above-described thin film as the plaster that carrier material hides (kaschieren), and therefore also can in the longer time section, not use boldly.Through correspondingly covering, also can transfer to prepare with inconspicuous skin-color according to plaster of the present invention to substrate dyeing or with the pre-staining carrier.
Self-adhering type plaster according to the present invention can have any random shape and size, for example circle, rectangle, square etc.Particularly preferably, can cut into any random shape and size rightly through commercially available shears by user based on PIB with based on the plaster of WG, thereby make the accurately desired area for treatment of coupling of plaster according to of the present invention.
What shown is; When plaster with diameter≤20mm; Preferably≤15mm; The circle of preferred quite especially≤10mm is when elliptical shape exists, and the hydrogel matrix that is used in particular for treating local pigment over-deposit (like pigment over-deposit after senile plaque, sunburn, the inflammation) (for example being caused by pseudofolliculitis barbae (Pseudofollikulitis barbae)) according to the present invention is proved to be special easy operating and effective with polyisobutylene substrate.
Show, when plaster has>=25cm 2, preferred>=15cm 2, quite especially preferably>=4cm 2Area the time, be proved to be special easy operating and effectively according to the hydrogel matrix that is used in particular for treating local pigment over-deposit (like chloasma) of the present invention and polyisobutylene substrate.
The specific embodiment
Example:
Example 1: based on the wet adhesive film (FKF) of poly propenoic acid vinyl alcohol
Weight %
Polyvinyl alcohol 68.0
Polyacrylic acid 16.5
PEG400 9.5
Glycerol 5.0
The 4-n-butyl resorcinol 1.0
Example 2: based on the polarity anhydrous gel substrate (WFG) of poly propenoic acid vinylpyrrolidone
Weight %
Dexpanthenol 3.0
Propylene glycol 5.0
PEG400 18.0
Polyacrylic acid 22.5
Polyvinylpyrrolidone 3.5
Silicon dioxide 4.0
Glycerol 43.0
The 4-n-butyl resorcinol 1.0
Example 3: nonpolar polyisobutylene substrate (PIB)
Weight %
PIB?12 21.5
PIB?80 20.0
PIB?12 10.0
Cellulose 33.0
Isopropyl myristate 5.0
Ceraphyl 140 9.5
The 4-n-butyl resorcinol 1.0
Example 4: based on agar/polyacrylic polar water gel-type vehicle (WG)
Weight %
Water 49.1
Sorbitol 15.7
Agar 2.0
Glycerol 20.0
Polyacrylic acid 8.0
NaOH?45％ 4.2
The 4-n-butyl resorcinol 1.0

Claims (7)

1. transdermal therapeutic system, self-adhering type plane binder, particularly beauty treatment with and pharmaceutical plaster, it comprises the 4-n-butyl resorcinol as effective ingredient.
2. transdermal therapeutic system according to claim 1, self-adhering type plane binder, particularly beauty treatment are used and pharmaceutical plaster, it is characterized in that it exists as matrix system.
3. transdermal therapeutic system according to claim 2, self-adhering type plane binder, particularly beauty treatment are used and pharmaceutical plaster, it is characterized in that said substrate is selected from:
Based on non-polar substrate (KA) synthetic and natural rubber,
Based on the wet adhesive film (FKF) of the polarity of poly propenoic acid vinyl alcohol,
Based on the non-polar substrate (PAC) of acrylic copolymer,
Based on the polarity anhydrous gel substrate (WFG) of poly propenoic acid vinylpyrrolidone,
Nonpolar polyisobutylene substrate (PIB),
Based on agar/polyacrylic polar water gel-type vehicle (WG).
4. require each described transdermal therapeutic system according to aforesaid right; Self-adhering type plane binder, particularly beauty treatment are used and pharmaceutical plaster, it is characterized in that; It comprises the 0.001-10 weight % of the main assembly that accounts for preparation, the 4-n-butyl resorcinol of preferred especially 0.01-1 weight %.
5. require each described transdermal therapeutic system according to aforesaid right; Self-adhering type plane binder, particularly beauty treatment are used and pharmaceutical plaster, it is characterized in that; Preparation comprises the 0.001-10 weight % of the main assembly that accounts for preparation; Preferred especially 0.01-7.5 weight %, penetrating agent, particularly isopropyl palmitate and/or the isopropyl myristate of preferred quite especially 0.1-5 weight %.
6. require each described transdermal therapeutic system according to aforesaid right, it is characterized in that, it is＞30% that the effective ingredient of 4-n-butyl resorcinol was released in 24 hours, preferably is 55-65% in 24 hours.
7. require each described transdermal therapeutic system according to aforesaid right; Self-adhering type plane binder; Particularly beauty treatment is with disorderly in order to treat local pigmentation with pharmaceutical plaster; Particularly local pigment over-deposit is like pigment over-deposit after senile plaque, sunburn, the inflammation (for example being caused by pseudofolliculitis barbae (Pseudofollikulitis barbae)), chloasma.
CN2010800454733A 2009-10-09 2010-07-14 Transdermal therapeutic system comprising 4-n-butylresorcinol Pending CN102573817A (en)

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DE102009048973A DE102009048973A1 (en) 2009-10-09 2009-10-09 Transdermal therapeutic systems containing 4-n-butylresorcinol
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